OXIDATION OF MESITYLENE BY HYDROGEN PEROXIDE IN AcOH-Ac2O-H2SO4

Article abstract of DOI:10.1007/BF01184518

By the oxidation of mesitylene by hydrogen peroxide in AcOH-Ac2O-H2SO4 one can obtain mesitol (2,4,6-trimethylphenol) with a selectivity of 57-69percent at a mesitylene conversion of 22-16percent and the acetate of mesitol with a selectivity of 72-85percent at 25-22percent conversion.The peroxide responsible for the oxidation of mesitylene in this system is in the form of peracetic acid, formed in situ.Over the concentration range studied, the reaction is first order in AcOOH, mesitylene, and H2SO4.Hydroxylation of mesitylene by AcOOH proceeds by an electrophilic substitution mechanism, the limiting step being the formation of the ?-complex.